Why I Always Talk About My Ex On First Dates

Honesty is the best policy, right?

Kasandra Brabaw

Dec 19, 2018 | 2:00 PM

Photo by Hayden Williams/Stocksy

In New York City, asking someone how many roommates they have is akin to saying, “So, how about all this rain?” When the conversation has no where else to turn, New Yorkers bring up housing (curse those tiny, expensive apartments). Unfortunately for me, first dates are all about this kind of small talk, which means I’m forever telling could-be-girlfriends that I live with my ex.

It typically goes like this: Between sips of pinot grigio, she asks The Question: “Do you have any roommates?” My mind goes into hyperdrive as I think, Should I tell her about Katie? If I tell her I have a roommate but leave out that she’s my ex, that’s not really lying. But what if this starts getting serious? Is it worse to say it now and risk freaking her out or to say it later and look like I’m hiding something?

Inevitably, I end up telling the whole, uncomfortable truth. I live with my ex-girlfriend, and not even because I have to. I live with her because she’s my best friend and the only person I’d want to share 600 square feet and a kitchen the size of a closet with. As much as it may sound like I’m living in a fantasy land where unicorns replace taxi cabs, the clouds are made of cotton candy, and people can be best friends with their exes, there really isn’t any drama between me and Katie (and no lingering romantic feelings, either). So no, I really don’t have anything to hide. But that doesn’t make talking about my ex on first dates any less terrifying.

Cultural rules about dating always say that bringing up your ex is a big no-no. As general wisdom goes, someone who talks about their ex early on is clearly still harboring romantic feelings. So what do the women I’ve dated think about me living with Katie?

Surprisingly, my confession has never been a big deal. Once I get past the awkward monologue in my head, the rest of the date tends to go smoothly. Don’t get me wrong — most women are surprised by my living situation, but they’re not turned off (at least, they don’t tell me if they are). I’d like to use this as proof that queer women are so much cooler than straight men, who’d clearly freak out at this tidbit of information, but I can’t. Katie has been on plenty of dates with straight men who don’t care that she lives with her ex, either. (Maybe they’d care if I were a dude, because then I’d be threatening their masculinity. But again, that’s just a guess.)

So what’s up with this carefree attitude Katie and I have both witnessed from our dates? Maybe people are finally ditching those antiquated dating rules that try to enforce what you can talk about when. Maybe New Yorkers are just much more chill than most about who you live with. But Katie and I like to think it’s all in how we tell the story.

Sure, we used to date. But we broke up three-and-a-half years ago, and stopped being sexually attracted to each other long before that. Toward the end of our relationship, Katie and I had already transformed from girlfriends into girl friends — we just had to acknowledge it and find a new way forward. When Katie (who has always been the brave one) finally said, “We need to talk,” we both felt good about the split. From that day on, you could almost erase our romantic history. It felt like Katie had always been the Christina to my Meredith or the Willow to my Buffy. She’s my person, my best friend, and my family.

Luckily for me, the people who matter understand and respect our relationship. My first date with my current girlfriend went almost exactly like every other first date, except she asked The Question over beer instead of pinot grigio. But even though I was just as terrified as always, I didn’t have anything to worry about. She told me later that she thought it was a little strange that I live with my ex, but she also saw my ability to cherish a relationship with an ex as evidence that I was exactly the kind of person she’d want to date.